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Bridging the Gap: Music Stars in Gap Ads - Hip hop continues to break down walls. Nas and his father, jazz-blues musician Olu Dara, are featured together in a new Gap holiday ad campaign called "Love Comes in Every Shade." Their ad and poster, called "Fatherly Love," features them embracing. It's another impactful ad for Gap, which was an early adopter in embracing hip hop and soul stars for its marketing. Click on to check out some of the other music stars who have appeared in landmark ads for the apparel company. (Photo: Courtesy Gap)

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Lenny Kravitz - Lenny Kravitz was featured in a 2004 ad for Gap, which showed him playing his hit song "Lady" and dancing around with Sarah Jessica Parker. (Photo: Courtesy Gap)

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Estelle - A dapper Estelle appeared in a 2009 holiday-themed print campaign for Gap.  (Photo: Courtesy Gap)

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Common  - Good thing Common made this cuddly commercial, "Holiday in Your Hood," years before he clashed with Drake last winter. The 2007 ad features Common standing atop a large peace sign and rapping, "love, peace and Gap." So sweet. (Photo: Courtesy Gap)

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Tweet - Missy Elliot protégé Tweet was featured in a Gap commercial alongside actress-singer Taryn Manning, belting out the Staple Singers classic "I'll Take You There." (Photo: Courtesy Gap)

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will.i.am - Does will.i.am actually make music anymore in between shooting all these commercials? In 2007, he was featured in a holiday print campaign for Gap. Of course. (Photo: Courtesy Gap)

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LL Cool J            - LL Cool J's raw 1997 ad was a breakthrough. It showed LL rhyming like his old self a capella — at a time when many brands were still hands off in terms of hip hop. But L also pulled a subversive fast one on his employers: Not only was he wearing a hat from upstart urban wear company Fubu in the ad, but he also slickly shouted the brand out in his verse. (Photo: Courtesy Gap)

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Flo Rida, Trey Songz and Friends - In Gap's bizarre 2008 holiday campaign, Flo Rida remixed "Jingle Bells" with help from Trey Songz, Janelle Monáe, the Dixie Chicks and more. (Photo: Courtesy Gap)

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Childish Gambino - Rapper Childish Gambino — aka actor-comedian Danny Glover — spoke about the importance of charity in a commercial for Gap's holiday campaign in 2010.  (Photo: Courtesy Gap)

Photo By Photo: Courtesy Gap

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Lena Horne    - The late, legendary Lena Horne sang "Winter Wonderland" in this charming 1997 ad for Gap. (Photo: Courtesy Gap)

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Run DMC - Run DMC repurposed their classic hit "Peter Piper" for this ingenious, old-school-inspired 1998 ad for Gap.  (Photo: Courtesy Gap)

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Madonna and Missy Elliott - Missy Elliott outshined Madonna on her own song (sort of) when the pair teamed up to resurrect the latter's hit "Get Into the Groove" in this 2003 commercial. (Photo: Courtesy Gap)

Photo By Photo: Courtesy Gap